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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 230891Erstellt: 26. Oktober 2026

Hydrochloric Acid → 2'-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyloxy)-6'-hydroxyacetophenone

https://huagongshe.com/reaction/230891

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktHydrochloric AcidHCID 313—
EduktPotassium CarbonateHCID 11430—
Edukt2',6'-DihydroxyacetophenoneHCID 69687—
Eduktalpha-D-Glucopyranosyl bromide, tetraacetateHCID 101776—
KatalysatorBenzyltributylammonium chlorideHCID 159952—
LösungsmittelWaterHCID 962—
LösungsmittelChloroformHCID 6212—
Produkt2'-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyloxy)-6'-hydroxyacetophenoneHCID 1055279443,6%

Reaktionsschritte

To a mixture of 2′,6′-dihydroxyacetophenone (1 g), potassium carbonate (4.54 g) and benzyltri(n-butyl)ammonium chloride (0.41 g) in chloroform (13 mL) were added water (0.5 mL) and acetobromo-α-D-glucose (2.7 g), and the mixture was stirred at room temperature for 24 hours. The reaction mixture was poured into water, and the mixture was acidified by addition of 2 mol/L hydrochloric acid. The resulting mixture was extracted with ethyl acetate, and the extract was washed with water and brine. The extract was dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue was treated with methanol, and the precipitated crystals were collected by filtration and dried under reduced pressure to give the title compound (1.38 g).

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS07566699B2
Quelldatensatzuspto-grants-2009_07
ORD IDord-9d240b3dce7d47339874ef7064ae6587
Quellennotizuspto-grants-2009_07